- Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides
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Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.
- Bhuyan, Samuzal,Chhetri, Karan,Hossain, Jagir,Jana, Saibal,Mandal, Susanta,Roy, Biswajit Gopal
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p. 5049 - 5055
(2021/07/29)
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- 2 - (1 H) - quinoline compound of microwave-assisted synthesis method (by machine translation)
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The invention belongs to the field of organic intermediate synthesis, in particular discloses a 2 - (1 H) - quinoline compound of microwave-assisted synthetic method: quinoline raw material, and water in a reaction promoter and microwave under the assistance of the addition reaction, to obtain the 2 - (1 H) - quinoline compound; the quinoline raw material is quinoline, or on the quinoline ring in addition to the 2 other than the position of the substituent on the quinoline derivatives containing; the reaction accelerator is 2 - chloroethyl ester and/or 2 - [...] ester. The method raw materials are easy, simple reaction conditions, the reaction time is short, green energy-saving, reaction selectivity and high yield, excellent substrate functional group compatibility, and has high application value. (by machine translation)
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Paragraph 0075; 0076
(2018/09/28)
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- Selectfluor-mediated regioselective nucleophilic functionalization of N-heterocycles under metal- and base-free conditions
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A practical and environmentally attractive methodology for the direct diversification of N-heterocycles at ambient temperature under open-air conditions was developed. The obvious advantage of the process is that no toxic reagent, transition metal, base or other additive is employed, thus greatly reducing costs, facilitating post-reaction neutralization and purification and minimizing the environmental impact.
- Xie, Long-Yong,Qu, Jie,Peng, Sha,Liu, Kai-Jian,Wang, Zheng,Ding, Man-Hua,Wang, Yi,Cao, Zhong,He, Wei-Min
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supporting information
p. 760 - 764
(2018/02/14)
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- Scalable and Practical Synthesis of Halo Quinolin-2(1H)-ones and Quinolines
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A practical and scalable synthesis of halo quinolin-2(1H)-ones is presented. The heterocycles are easily accessed from inexpensive halo anilines in a two-step sequence. The anilines are acylated with methyl 3,3-dimethoxypropionate under basic conditions in quantitative yields. The crude amides undergo cyclization in sulfuric acid to the desired halo quinolin-2(1H)-ones in 28-93% yield (2 steps). The synthetic sequence was successfully applied on 800 g scale. Anilines with strong electron withdrawing or electron donating groups were poor substrates for this procedure. 6-Iodoquinolin-2(1H)-one and 6-bromo-8-iodoquinolin-2(1H)-one were further functionalized to obtain quinolines substituted with various functional groups.
- Zaugg, Cornelia,Schmidt, Gunther,Abele, Stefan
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supporting information
p. 1003 - 1011
(2017/07/26)
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- 6-Cyano Analogues of Bedaquiline as Less Lipophilic and Potentially Safer Diarylquinolines for Tuberculosis
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Bedaquiline (1) is a new drug for tuberculosis and the first of the diarylquinoline class. It demonstrates excellent efficacy against TB but induces phospholipidosis at high doses, has a long terminal elimination half-life (due to its high lipophilicity), and exhibits potent hERG channel inhibition, resulting in clinical QTc interval prolongation. A number of structural ring A analogues of bedaquiline have been prepared and evaluated for their anti-M.tb activity (MIC90), with a view to their possible application as less lipophilic second generation compounds. It was previously observed that a range of 6-substituted analogues of 1 demonstrated a positive correlation between potency (MIC90) toward M.tb and drug lipophilicity. Contrary to this trend, we discovered, by virtue of a clogP/M.tb score, that a 6-cyano (CN) substituent provides a substantial reduction in lipophilicity with only modest effects on MIC values, suggesting this substituent as a useful tool in the search for effective and safer analogues of 1.
- Tong, Amy S. T.,Choi, Peter J.,Blaser, Adrian,Sutherland, Hamish S.,Tsang, Sophia K. Y.,Guillemont, Jerome,Motte, Magali,Cooper, Christopher B.,Andries, Koen,Van Den Broeck, Walter,Franzblau, Scott G.,Upton, Anna M.,Denny, William A.,Palmer, Brian D.,Conole, Daniel
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p. 1019 - 1024
(2017/10/18)
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- Iron-catalyzed aerobic oxidative cleavage of the C-C σ-bond using air as the oxidant: Chemoselective synthesis of carbon chain-shortened aldehydes, ketones and 1,2-dicarbonyl compounds
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A simple iron-catalyzed aerobic oxidative C-C σ-bond cleavage of ketones has been developed. Readily available and environmentally benign air is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, chemoselectively yielding carbon chain-shortened aldehydes, ketones and 1,2-dicarbonyl compounds without overoxidation.
- Xing, Qi,Lv, Hui,Xia, Chungu,Li, Fuwei
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p. 489 - 492
(2016/01/12)
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- Practical route to 2-quinolinones via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade reaction
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Quinolinone derivatives were constructed via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade process with simple anilines as the substrates. This finding provides a practical procedure for the synthesis of quinolinone-containing alkaloids and drug molecules. The utility of this method was demonstrated by a formal synthesis of Tipifarnib.
- Wu, Junliang,Xiang, Shaohua,Zeng, Jing,Leow, Minli,Liu, Xue-Wei
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supporting information
p. 222 - 225
(2015/01/30)
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- Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: An efficient route to 2-quinolinones
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A Ru-catalyzed cyclization of anilides with propiolates or acrylates affording 2-quinolinones having diverse functional groups in good to excellent yields is described. Later, 2-quinolinones were converted into 3-halo-2-quinolinones and 2-chloroquinolines
- Manikandan, Rajendran,Jeganmohan, Masilamani
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supporting information
p. 3568 - 3571
(2014/07/21)
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- NOVEL NITROGENATED HETEROCYCLIC COMPOUND AND SALT THEREOF
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A nitrogen-containing heterocyclic compound represented by the general formula: wherein the dashed line represents a single bond or a double bond; R1, R2, R3, R4 and R5 independently represent a hydrogen atom, halogen atom, a lower alkyl, aryl, lower alkoxy or monocyclic heterocyclic group which may be substituted or the like; R6 represents a lower alkyl, aryl, monocyclic heterocyclic, bicyclic heterocyclic or tricyclic heterocyclic group which may be substituted; X1 represents a lower alkylene group or the like; X2 represents a lower alkylene, lower alkenylene or lower alkynylene group which may be substituted; X3 represents an oxygen atom, sulfur atom, a sulfinyl group, sulfonyl group or the like; Y1 represents a bivalent cyclic group, containing a nitrogen, which may be substituted or the like; and Z1 represents a nitrogen atom, a carbon atom which may be substituted or the like, or a salt thereof. The compound or salt has a potent antibacterial activity and a high safety, and is therefore useful as an excellent antibacterial agent.
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- II. Synthesis and biological evaluation of some bioisosteres and congeners of the antitumor agent, 2-{4-[(7-chloro-2-quinoxalinyl)oxylphenoxy}propionic acid (XK469)
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XK469 (1) is among the most highly and broadly active antitumor agents to have been evaluated in our laboratories. Subsequent developmental studies led to the entry of (R)-(+) 1 (NSC 698215) into phase 1 clinical trials (NIH UO1-CA62487). The antitumor me
- Hazeldine, Stuart T.,Polin, Lisa,Kushner, Juiwanna,White, Kathryn,Bouregeois, Nicole M.,Crantz, Brianna,Palomino, Eduardo,Corbett, Thomas H.,Horwitz, Jerome P.
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p. 3130 - 3137
(2007/10/03)
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- A General Approach to the Synthesis of 1,6-, 1,7-, and 1,8-Naphthyridines
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A new three-step procedure for pyridine annulation is described and illustrated with efficient syntheses of various 1,6-, 1,7-, and 1,8-naphthyridin-2-ones as well as 6-chloroquinolin-2-one.The regiospecific ortho metalation and subsequent formylation of
- Turner, James A.
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p. 4744 - 4750
(2007/10/02)
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